SYNTHESIS AND CHARACTERIZATION OF CYCLIZED DONOR-ACCEPTOR CYANOARENE PHOTOCATALYSTS

In a Ni-catalyzed visible light-promoted C–N cross-coupling study,1 the commercial cyanoarene photocatalyst 3DPA2FBN yielded two by-products under blue light, identified by HPLC–MS as mono- and bis-cyclized products from the loss of 1 or 2 HF molecules. As PC photodegradation products often retain photocatalytic activity,2 we synthesized these 3DPA2FBN cyclization derivatives, fully characterizing and testing them as PCs. 1D/2D NMR and XRD elucidated the structures of the isolated regioisomers. Electrochemical and spectroscopic techniques determined the photophysical properties of 1 and 2, then tested in various reactivities. Additionally, a regioisomeric mono-cyclized product 3 was isolated and characterized, and proved to be the precursor of 2.